First 1099-DA season: check how your software handled transfers to your own wallets before you file
Something I keep seeing now that 1099-DA forms are in play: transfers between your own wallets getting booked as taxable disposals.
The pattern: you move coins from an exchange to your own cold wallet, or between two wallets you control. Your tax software doesn't know the receiving address is yours, so it treats the send as a sale at fair market value. If the coin appreciated since you bought it, that's a phantom gain — tax owed on money you never actually realized.
I went down this rabbit hole after running standard cost-basis rules across a set of wallets that are publicly known to belong to one person, twice: once treating them as one owner, once as strangers. Same chain data, roughly $45M of difference in "gains". The only thing that changed was the ownership assumption.
What I'd check before filing:
- Write down every address you control, including old ones you barely use.
- In your software's transaction list, filter for disposals that have no fiat or stablecoin proceeds. Those are the suspects.
- For each suspect, look up the tx hash in a block explorer and check whether the receiving address is on your list. If it is, it should be a transfer (basis carries over), not a sale.
- Bridges and exchange internal moves are where tools misread the most.
Disclosure: I build verification tooling in this space, which is why I stare at this failure mode a lot. No links here on purpose — the checklist works with whatever software you already use.
Has anyone's software or 1099-DA actually matched self-transfers correctly this year? Curious what people are seeing.